Help keep this site alive with your VIP membership and unlock exciting site features available only to our supporting members!
UPGRADE to get lifetime access to dig420's video section, the Meet Up! forums, AD FREE surfing and much, much more!
What's your biggest ever sexual regret?
- Thread starterSwingingChris
- Start date
My wife was regular fucked by two other guys in a 3some what i was not aware of in beginning.
When i met her she became my girlfriend and ofcourse i fucked her.
But ... she did not quit fucking these two other guys and fucked them behind my back.
I confronted her with it and she she was ashamed and did quit it.
So my regret is i accepted her excuse and accepted she did quit fucking them.
I should have encourige her to continou and made a even bigger slut of her.
When i met her she became my girlfriend and ofcourse i fucked her.
But ... she did not quit fucking these two other guys and fucked them behind my back.
I confronted her with it and she she was ashamed and did quit it.
So my regret is i accepted her excuse and accepted she did quit fucking them.
I should have encourige her to continou and made a even bigger slut of her.
I have three:
1. My wife was my first. I was 17 and she was a hot 25-year old and we fucked like rabbits. I was obviously not her first, second, third, fourth, fifth, etc. I recall fucking her nine times one day. Just couldn't get enough of her. When we got engaged years later, she asked me if I wanted to fuck someone else so that I'd be sure and not want to fuck someone else when we were married. I thought it was a test, so I said no she was all the woman I need. I should have said, "Well........that's a smart idea."
2. I was newly married and in love with my wife. Back then, I thought I outkicked my coverage getting her. I was working with a beautiful girl just out of college who was a former college cheerleader and was a Miss Pennsylvania contestant. She looked like a Dallas Cowboys cheerleader. We went to lunch together and one day while waiting to go through the drive through, her face was really close to mine. I paused and backed up. Dumb. This same woman invited me to her place on Christmas Eve which wouldn't have been easy to explain why I wasn't home for Christmas Eve, but had I known my marriage would have ended in a divorce......
3. After being married a few years, it seemed like I was always the one initiating sex. Not that she ever said no, but I thought it would be nice if she would initiate it once in a while. So I wanted to see how long she could go without it. It was going on two weeks and she finally said to me, "If you're not going to fuck me, I'll go out and find someone that will." I was so turned on hearing her talk like that I had to fuck her twice right then. I should have held off and had her go out and become the hot slut wife I later wanted so bad.
1. My wife was my first. I was 17 and she was a hot 25-year old and we fucked like rabbits. I was obviously not her first, second, third, fourth, fifth, etc. I recall fucking her nine times one day. Just couldn't get enough of her. When we got engaged years later, she asked me if I wanted to fuck someone else so that I'd be sure and not want to fuck someone else when we were married. I thought it was a test, so I said no she was all the woman I need. I should have said, "Well........that's a smart idea."
2. I was newly married and in love with my wife. Back then, I thought I outkicked my coverage getting her. I was working with a beautiful girl just out of college who was a former college cheerleader and was a Miss Pennsylvania contestant. She looked like a Dallas Cowboys cheerleader. We went to lunch together and one day while waiting to go through the drive through, her face was really close to mine. I paused and backed up. Dumb. This same woman invited me to her place on Christmas Eve which wouldn't have been easy to explain why I wasn't home for Christmas Eve, but had I known my marriage would have ended in a divorce......
3. After being married a few years, it seemed like I was always the one initiating sex. Not that she ever said no, but I thought it would be nice if she would initiate it once in a while. So I wanted to see how long she could go without it. It was going on two weeks and she finally said to me, "If you're not going to fuck me, I'll go out and find someone that will." I was so turned on hearing her talk like that I had to fuck her twice right then. I should have held off and had her go out and become the hot slut wife I later wanted so bad.
Hindsight is a wonderful thing, so i wouldnt alter anything really as any change could have altered our marriage and i consider myself lucky to have remained married to a women who has been extremely kinky over the years, made me her true cuck husband early on in our marriage and still enjoys a bit of fun.
However thats a boring answer.
So onto my wish list!
Things i wish i had done;
I wish i had taken a sweet innocent virgin when i was 18 up on her offer at college to sleep with her, god i was so naive, she dropped so many hints they would have broken my toes, still i ignore her offers: she was 17 very nice and sweet with a lovely body and certainly marrying material so that may have changed things.
I wish i had taken advice from an older married womaniser friend to stop looking at the firm jean clad teenage girls and look at their easier mothers, they could have taught me so much, he even pointed out a few in a pub we used go to, that kept looking at me and he knew they were interested. It later dawned on me that whilst i knew i couldnt satisfy them they could have taught me how to. Then i would have been a better lover, but then would my young wife have cheated on me and made me her cuck? as she has said, yes i probably would have anyway as she likes the touch and feel of other men.
I wish that my cuckoldress who can be very kinky and exceptionally naughty and likes having lovers and exploring and expanding her sexuality, yet 95% of the time is so straight laced, prim and proper she could be a nun. How i wish was she 80% straight laced and 20% kinky.
That in our 20s. 30s and onwards i didnt take my cuckoldress to more places where there were more opportunites for her to meet men, easy said, difficult because of our jobs and weighed down by kids.
My biggest and this is a BIG regret is:
We knew a couple, i worked at the same place as him, he was so boring she was so sexy and super fit and i knew very kinky (from experience). We went one night to their house where we were then told to go to the pub and not comeback until told? WTF.
He told me he had done this before and she would be annoyed if we went back univited, as she was "entertaining", entertaining??? he wouldnt explain ,so we had a few pints. I am not used to being told what to do and several hours later i insisted we go back at the back he was boring me to death too. I also kept dreaming has she arranged for men to visit them?. i hoped so we had left them drinking so she would without a doubt be receptive how exciting....
Looking through the crack in the curtains i have never been so shocked ever...
My wife was naked apart from her knickers she was bent over his wife sucking her tits, she was naked.
We went in, he didnt want to, the smell of cannabis hit me immediately, i comtinued into the front room like some fool, his wife was fingering mine as my wife sat back up, obviously spaced out and ***** she continued fingering my wife for a few seconds then pulled out as my wife gasped and then got dressed.
So i fucked that up. We left soon after.
I went to see his wife that week when he was at work:
I knew her quite well and she told me my wife wanted lessons in lady love and was easy and receptive to being taught, she had shown no hesitation about try this and took her own clothes off soon after they had a joint. She told me that they had arrange another night when us men were working and told me your working nights on saturday arent you? Yes i was.........OMG. She said my wife had messaged confirming she was still attending Saturday.
She took me to her bedroom and showed me toys she would use and pointing to a set of drawers said, would you like a video of us together? what.....WOW, i replied i didnt think she would like this, she replied oh she would.
This changed my view of my cuckoldress though i dont this other women knew she was my cuckoldress.
However.... whilst my cuckoldress never mentioned this, it went spectacularly pair shaped during the week, my cuckoldress without invite went round for a brew thinking she would be in and was confronted by her husband, he was nasty and sharp with her for calling.
That distroyed that.
Later i visited her to seek an explanation of why this had happened, she blamed my wife for just arriving and her husband for over reacting, she said she had hours earlier told him about Saturday so he didnt pop home from work and HE assumed i was going too.
However thats a boring answer.
So onto my wish list!
Things i wish i had done;
I wish i had taken a sweet innocent virgin when i was 18 up on her offer at college to sleep with her, god i was so naive, she dropped so many hints they would have broken my toes, still i ignore her offers: she was 17 very nice and sweet with a lovely body and certainly marrying material so that may have changed things.
I wish i had taken advice from an older married womaniser friend to stop looking at the firm jean clad teenage girls and look at their easier mothers, they could have taught me so much, he even pointed out a few in a pub we used go to, that kept looking at me and he knew they were interested. It later dawned on me that whilst i knew i couldnt satisfy them they could have taught me how to. Then i would have been a better lover, but then would my young wife have cheated on me and made me her cuck? as she has said, yes i probably would have anyway as she likes the touch and feel of other men.
I wish that my cuckoldress who can be very kinky and exceptionally naughty and likes having lovers and exploring and expanding her sexuality, yet 95% of the time is so straight laced, prim and proper she could be a nun. How i wish was she 80% straight laced and 20% kinky.
That in our 20s. 30s and onwards i didnt take my cuckoldress to more places where there were more opportunites for her to meet men, easy said, difficult because of our jobs and weighed down by kids.
My biggest and this is a BIG regret is:
We knew a couple, i worked at the same place as him, he was so boring she was so sexy and super fit and i knew very kinky (from experience). We went one night to their house where we were then told to go to the pub and not comeback until told? WTF.
He told me he had done this before and she would be annoyed if we went back univited, as she was "entertaining", entertaining??? he wouldnt explain ,so we had a few pints. I am not used to being told what to do and several hours later i insisted we go back at the back he was boring me to death too. I also kept dreaming has she arranged for men to visit them?. i hoped so we had left them drinking so she would without a doubt be receptive how exciting....
Looking through the crack in the curtains i have never been so shocked ever...
My wife was naked apart from her knickers she was bent over his wife sucking her tits, she was naked.
We went in, he didnt want to, the smell of cannabis hit me immediately, i comtinued into the front room like some fool, his wife was fingering mine as my wife sat back up, obviously spaced out and ***** she continued fingering my wife for a few seconds then pulled out as my wife gasped and then got dressed.
So i fucked that up. We left soon after.
I went to see his wife that week when he was at work:
I knew her quite well and she told me my wife wanted lessons in lady love and was easy and receptive to being taught, she had shown no hesitation about try this and took her own clothes off soon after they had a joint. She told me that they had arrange another night when us men were working and told me your working nights on saturday arent you? Yes i was.........OMG. She said my wife had messaged confirming she was still attending Saturday.
She took me to her bedroom and showed me toys she would use and pointing to a set of drawers said, would you like a video of us together? what.....WOW, i replied i didnt think she would like this, she replied oh she would.
This changed my view of my cuckoldress though i dont this other women knew she was my cuckoldress.
However.... whilst my cuckoldress never mentioned this, it went spectacularly pair shaped during the week, my cuckoldress without invite went round for a brew thinking she would be in and was confronted by her husband, he was nasty and sharp with her for calling.
That distroyed that.
Later i visited her to seek an explanation of why this had happened, she blamed my wife for just arriving and her husband for over reacting, she said she had hours earlier told him about Saturday so he didnt pop home from work and HE assumed i was going too.
When a teenage friend tried to wank me off I was so startled and shocked I kicked him out.
Years later I discovered my bi sexuality and have regretted missing out on so much pleasure ever since. Nothing can beat being taken and having my man pussie filled to overflowing with tasty hot cum.
Years later I discovered my bi sexuality and have regretted missing out on so much pleasure ever since. Nothing can beat being taken and having my man pussie filled to overflowing with tasty hot cum.
Last edited:
I have a few regrets not for what I did but what I didn’t , one was not realising early my wife wanted to fuck my best friend , also not saying yes to me sharing their bed one night , don’t ask why I have no idea I think I thought it was a trick . I had the chance to fuck her friend Libby but was to scared to go through with it , Kate was at the time messing around with her husband I think I did see them in a passionate kiss one New Year’s Eve
